2014
DOI: 10.1002/jlcr.3195
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Synthesis and evaluation of a new 99mTc(I)‐tricarbonyl complex bearing the 5‐nitroimidazol‐1‐yl moiety as potential hypoxia imaging agent

Abstract: The objective of this work was to develop a novel (99m) Tc complex bearing the 5-nitroimidazol-1-yl moiety with recognised selectivity towards hypoxic tissue, as a potential radiopharmaceutical for imaging tumour hypoxia. The new metronidazole derivative (2-amine-3-[2-(2-methyl-5-nitro-1H-imidazol-1-yl)ethylthio]propanoic acid) (L) containing adequate groups to coordinate technetium through the formation of a Tc(I)-tricarbonyl complex was synthesised with adequate yield (33%) and characterised by spectroscopy.… Show more

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Cited by 19 publications
(11 citation statements)
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“…Although 2-nitroimidazoles have been preferred as redox centres in Tc complexes targeting hypoxia, 5-nitroimidazoles derived from metronidazole have also demonstrated high affinity for hypoxic tumours "in vitro" and "in vivo" and have been labelled by the formation of [ 99m Tc]Tc-(CO) 3 complexes. Giglio et al [41] have prepared a cysteine-derivative that bears an NSO type-chelator unit in which the donor atom system consists of an N-primary amine, an S-thioether and an O-carboxylate. The Tc complex was neutral but the log P o/w was −0.75 since the incorporation of a cysteine moiety reduced the lipophilicity.…”
Section: Labelling Strategies Of Nitroimidazoles With [ 99m Tc]tcmentioning
confidence: 99%
See 1 more Smart Citation
“…Although 2-nitroimidazoles have been preferred as redox centres in Tc complexes targeting hypoxia, 5-nitroimidazoles derived from metronidazole have also demonstrated high affinity for hypoxic tumours "in vitro" and "in vivo" and have been labelled by the formation of [ 99m Tc]Tc-(CO) 3 complexes. Giglio et al [41] have prepared a cysteine-derivative that bears an NSO type-chelator unit in which the donor atom system consists of an N-primary amine, an S-thioether and an O-carboxylate. The Tc complex was neutral but the log P o/w was −0.75 since the incorporation of a cysteine moiety reduced the lipophilicity.…”
Section: Labelling Strategies Of Nitroimidazoles With [ 99m Tc]tcmentioning
confidence: 99%
“…Structure of imidazole derivatives used in the preparation of [ 99m Tc]Tc-tricarbonyl complexes[37][38][39][40][41][42].…”
mentioning
confidence: 99%
“…IR (KBr, cm The rhenium analogue of 4-nitroimidazole-triazole-[ 99m Tc(CO) 3 ] was prepared by refluxing a mixture of 4-nitroimidazole-triazole (0.17 g, 0.55 mmol) and bis(tetraethylammonium)-fac-tribromotricarbonylrhenate (0.42 g, 0.55 mmol) in 5 mL water for 15 h [27]. The compound bis(tetraethylammonium)-fac-tribromotricarbonylrhenate was prepared following a procedure reported by Alberto et al [28]. After refluxing, reaction mixture was allowed to cool down and then filtered.…”
Section: Synthesis Of 1-(3-azidopropyl)-5-nitro-1h-imidazole (6)mentioning
confidence: 99%
“…Nitroimidazoles which show selective accumulation in hypoxic cells are the most widely explored molecules for delineating hypoxic tumor cells from normoxic cells [10]. Several nitroimidazole radiopharmaceuticals based on PET as well as SPECT isotopes are reported [11][12][13][14][15][16][17][18][19][20][21][22][23][24][25][26][27][28]. Presently, [ 18 F]fluoromisonidazole ([ 18 F]FMISO), a 2-nitroimidazole-radiotracer, is the radiopharmaceutical of choice for clinical imaging of tumor hypoxia [29].…”
Section: Introductionmentioning
confidence: 99%
“…Nevertheless, these hypoxia markers contained several limitations such as selectivity deficiency and excessive background signal of blood [ 5 ]. As a result of this, alternative compounds that are able to identify tumor hypoxia and overcome these limitations may provide additional assistance [ 7 ]. The 5-nitroimidazole metronidazole with high affinity for hypoxic tumors in vitro and in vivo is one of the potential hypoxia makers, and it is considered to be the original material for preparing 99m Tc radiopharmaceuticals [ 8 ].…”
Section: Introductionmentioning
confidence: 99%